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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27N3O3S
Molecular Weight 401.522
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SONEPIPRAZOLE

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N2CCN(CC[C@@H]3OCCC4=C3C=CC=C4)CC2

InChI

InChIKey=WNUQCGWXPNGORO-NRFANRHFSA-N
InChI=1S/C21H27N3O3S/c22-28(25,26)19-7-5-18(6-8-19)24-14-12-23(13-15-24)11-9-21-20-4-2-1-3-17(20)10-16-27-21/h1-8,21H,9-16H2,(H2,22,25,26)/t21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H27N3O3S
Molecular Weight 401.522
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10989267

Sonepiprazole exhibits highly specific binding to the D4 dopamine receptor with more than 100-fold selectivity for the D4 receptor over other receptors, including dopamine, serotonin, and adrenergic receptors. It is a neutral antagonist at the D4 dopamine receptor and is devoid of dopamine agonist activity. Sonepiprazole selectively induces c-fos expression in the prefrontal cortex and blocks behavioral, biochemical, and genomic effects of repeated amphetamine administration in rats. Sonepiprazole was investigated as an antipsychotic for the treatment of schizophrenia in a placebo-controlled clinical trial, but in contrast to its comparator olanzapine no benefits were found and it was not researched further for this indication.

CNS Activity

Curator's Comment: The induction of c-fos mRNA in the rat medial prefrontal cortex, the blockade of amphetamine-induced behavioral sensitization and associated genomic changes, and the cognitive effects of sonepiprazole in nonhuman primates all provide evidence of central nervous system (CNS) penetration of the drug at peripherally administered doses of as low as 0.1 mg/kg.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a common receptor microdomain.
2004 Dec
WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation.
2009 Feb
Patents

Patents

Sample Use Guides

1 capsule containing sonepiprazole (1.5, 10, or 60 mg) once daily in the morning.
Route of Administration: Oral
In the presence of Sonepiprazole (10 uM; 3 min exposure duration), six of nine murine neurons displayed an increased frequency of spontaneous inward currents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:37 GMT 2023
Record UNII
O609V24217
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SONEPIPRAZOLE
INN   WHO-DD  
INN  
Official Name English
(-)-P-(4-(2-((S)-1-ISOCHROMANYL)ETHYL)-1-PIPERAZINYL)BENZENESULFONAMIDE
Common Name English
Sonepiprazole [WHO-DD]
Common Name English
(S)-4-(4-(2-(3,4-DIHYDRO-1H-2-BENZOPYRAN-1-YL)ETHYL)-1-PIPERAZINYL)BENZENESULFONAMIDE
Systematic Name English
sonepiprazole [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
Code System Code Type Description
SMS_ID
100000084956
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
EVMPD
SUB04508MIG
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID801317650
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
PUBCHEM
133079
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
NCI_THESAURUS
C73294
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
FDA UNII
O609V24217
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
MESH
C100448
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL69759
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
CAS
170858-33-0
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
INN
7799
Created by admin on Fri Dec 15 15:50:37 GMT 2023 , Edited by admin on Fri Dec 15 15:50:37 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY